Epic Gravel Tuscany

Epic Gravel Tuscany

Epic Gravel Tuscany

Tuscany - Guided

Guided  Gravel Tuscany  Bike Tour

Ride the famous ‘strade bianche’ white gravel roads of Tuscany, explore the medieval towns and enjoy world-famous Tuscan food and wine on this dream trip – join one of our planned departure

Pienza in the heart of val d’Orcia

Montalcino brunello wine, Siena the Gotham gothic city and Gaiole the Eroica town… what else?

Wow Moments

  • Shadow the hilly path of L’Eroica, Tuscany’s internationally recognized vintage bike race
  • 3 King’s wines: Vino Nobile di Montepulciano, Brunello di Montalcino, Chianti classico
  • Explore the undulating white gravel roads of Tuscany—the famed strade bianche—and immerse yourself in Italy’s most classic cycling local
  • Stay one night at luxury wine relais in Montalcino: Mastrojanni and enjoy brunello wine experience

Strade Bianche of Tuscany

The Strade Bianche of Tuscany is truly something special due to the region’s rolling vistas and fine wines make this a must-see destination if you love gravel cycling. Strade bianche  is Italian for “white roads,” and it comes from the color of the dry limestone gravel that lifts into a fine white dust that lingers along the race course.

These white, dusted roads are home to one of pro racing’s biggest dates, with steep climbs and full-blown attacks at every bend:  Strade Bianche professional race

After the successful of our self guided Bike Tour in 2021 we decided to offer the guided version  selecting the more appropriate sections from  that race, from the Eroica itinerary that often coincide with Francigena path
The Permanent Route of L’Eroica is a unique experience that allows you to live the adventure of L’Eroica all year round,  anyway we offer the tour from March to November.
Traditional L’Eroica course  starts in the town of Gaiole on the first Sundays of October, anyway we love the Montalcino spring edition.

Hotels are all different experiences: old convent in Pienza, a wine producer relais in Montalcino, a villa in Siena and a castle in Gaiole

The pool at each hotels (except Siena) will be well appreciated after those epic day

This trip is designed for gravel bikes, You can Bring your non-strong partner: great trekking e-bike are available and suitable for the itinerary
Or non-riding partner along: we have guided daily activities available for non-riders.

Carbon frame GRAVEL bike or  E-bike are perfect to face this tour


2024 departures

SPRING May 3 -9

FALL September  6- 12


Pienza & Bagno Vignoni

Meet at Chiusi-Chianciano train station at 12.00 (a stop on all major Florence-Rome lines).
Transfer to Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza the “perfect town” is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets
Check into your rooms at your hotel, which occupies a 15th-century convent in the center of town.
At 15.00 Meet your guides during a bike-fitting session and get to know the rest of the group. OPTIONAL (depends on time taken in the bike fitting) short ride to Bagno Vignoni:
a thermal spa town that dates back to Roman times, and Madonna di Vita Leta chapel
Welcome dinner at la Bandita townhouse

Distance 25 km /15 miles
12 km asphalt and 13 km gravel – Easy to Moderate


Montepulciano & Vino Nobile

Your tour starts with a circular ride from Pienza.
You pedal through these corridors of proud cypress trees, the scenery may look familiar from such films as The Gladiator and The English Patient. Follow the gravel tracks off the beaten path through a timeless slice of Tuscany and enjoy the first espresso, overlooking the roads we just conquered. By lunchtime you’ll come to Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces.
After a light lunch you deserve a wine tasting at our favorite cellar juts out of town – cantine Dei or Montemercurio.
Relaxing a while sipping a glass of Nobile wine… it’s time to continue: next stop is the village of Monticchiello, the quintessential Tuscan hill town.

distance 51 km /31,5 miles : 17 km asphalt and 34 km gravel – moderate difficulty


Pieve a Salti & Brunello Land

To get from Pienza to Montalcino we select the sections of Eroica called Lucignano d’asso and Pieve A Salti. You leave Pienza and after 6 km on paved road you will take the white road toward Cosona and reach the little hamlet of Lucignano – a caffè espresso at the little shop emporio – is a must. Once you reach the paved road you ride only one km and start the other Eroica gravel section Pieve a Salti – so beautiful landscape. 9 km up and down in the rural countryside! arrive in Buonconvento by lunch time. Now you have to face the climb to the famed wine town of Montalcino Tuscany’s most celebrated wine region. a total of 10 km: 5 on paved and 5 km on gravel all through vineyards and wineries.
In Montacino enjoy a light lunch and we will introduce to this legendary story, at every year Welcome Brunello with special tile.
We ask you the last effort to get to Pass Lume spento, the higher point of Montalcino, and enjoy the downhill to the wine relais  where you will overnight.
Tonight dinner at Relais Mastrojanno pairing the dishes with rosso and Brunello they produce.

distance 48 km /25 miles: – km asphalt and – km gravel – moderate difficulty


Castiglion del Bosco & Siena

L’Eroica—meaning “The Heroic”—is a celebration of the golden age of cycling. The event takes place every October when thousands of hardened cyclists travel back in time to ride these gravel roads on primitive machines of the past. The heavy lugged-steel bikes with down-tube shifters and impossible gear ratios are no match for the red wine in the participant’s water bottles and the hardman mentality. Today, we’ll have our own taste of cycling’s heroic origins as we join one of the most beautiful gravel sections of L’Eroica
From Tavernelle reach Castiglion del bosco gravel section- Castiglion del bosco is the biggest brunello winery & farm belonging to Ferragamo, the famous Italian fashion designer – once in Bibbiano another section called la Piana and reach Murlo after 30 km- caffé & visit! shortly you will face another famous Eroica section to Radi, with some steep yet short up and down.
Light lunch is planned at Ville di Corsano
Now the last 12 km on secondary paved road to Siena Dinner at Babazuf

distance 58 km /35 miles: 32 km asphalt and 24 km gravel – moderate to challenge


Gaiole, the Eroica town

Today the destination is the town where the Eroica starts
After your gourmet breakfast, head out into magical Chianti. You will exit form Siena via a eroica gravel section Pieve a Bozzone, Vico dArbia making your way through wheat fields before we hit the vineyards of this celebrated wine region. Reach Pianella after 15 km. Form here you will take a long glourios section to Canonica A Cerreto, Vagliagli- all road through chianti classico vineyards – Counting castles and old hilltop hamlets! Get in Radda in Chianti for lunch time after 38 km ride – mostly gravel.
now you have only 8 km to Gaiole following the Eroica path via san donato in Perano and Vertine, 2 small enchanting borgo Lodging at the charming Hotel castello spaltenna
dinner on your own

distance 46 km /28,5 miles
12 km asphalt and 34 km gravel – moderate to challenge


Chianti hills – Castello di Brolio

Today is consecrated to explore all the villages and hamlet of Chianti Senese- start from your “castle di Spaltenna” in Gaiole and reach Castello di Brolio after 10 km – here the caffé at agribar in front of winery is a must: all cyclists, locals and visitors seems to meet there.
after you can ride into the gravel section of Eroica, is short and then you will ride on very secondary scenery roads until Castelnuovo Berardenga, it worth a visit and if you are there for lunch time offer many options.
Wine tasting Felsina
back to the saddle and encounter other small borgo: San Gusmé and villa a Sesta – back to Brolio: to return to Gaiole you have 2 options, one road downhill and flat so somewhat easy, or challenge uphill to Castagnoli, downhill to castello di Meleto. Farewell dinner at the castle

distance 54 km /33,5 miles 44 km asphalt and 10 km gravel – moderate to challenge


Arrivederci, a presto

Farewell breakfast at Spaltenna castle

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Tour start Pienza
Tour end Gaiole

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best period spring & fall

DIFFICULTY challenge



Tour Reviews

15 January 2024

Dear Giuliana, Marco, Panos and all,

Thank you so much for making our recent ride so wonderful. You were all so helpful during the entire process- from planning, and through the entire ride. We truly appreciate that you allowed our tour to go ahead with only the four of us. Marco, you were an amazing leader! Panos, you were such a support and encourager! The accommodations were amazing. The food was wonderful. I can truly say this was one of the most beautiful rides of my life!

Best wishes in your South American cycling!

We hope to see you again in the future, and we will highly recommend you to other cyclists!


Leave a Review

Price & Inclusions

Cost: Euro 3250   per person  – price based on double accommodations –

single supplement euro 850


6 nights in excellent  luxury five, four & three-star superior hotels
6 breakfasts,
2 wine tasting
4 dinners
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions
All Baggage transfers
Keepsake Cicloposse water bottle
Sales taxes


Not Included

Bike Rental per entire tour
Gravel or E-bike € 250

2024 departures

May 3 -9
September  6- 12

Villa STR – Siena

A converted 19th-century villa, Villa di STR retains its historical charm and ambiance. Recently renovated, the public areas showcase exquisite Italian classical design, complemented by a peaceful garden. Located within a 10-minute walk from Piazza del Campo.

Castello di Spaltenna – Gaiole in Chianti

Enjoy an exclusive experience at Castello di Spaltenna, nestled in the heart of Chianti Classico. Luxurious guestrooms offer mesmerizing views of the valley, situated just a few meters outside Giaole in Chianti.

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